Iron-catalyzed N-alkylation of azoles via cleavage of an sp3 C-H bond adjacent to a nitrogen atom.

Iron-catalyzed N-alkylation of azoles via cleavage of an sp3 C-H bond adjacent to a nitrogen atom.

The Journal of organic chemistry (2012-10-03)

Qinqin Xia, Wanzhi Chen

ABSTRACT

Iron-catalyzed direct C-N bond formation between azoles and amides is described. The oxidative coupling reactions of sp(3) C-H bonds adjacent to a nitrogen atom in amides and sulfonamides with the N-H bond in azoles proceeded smoothly in the presence of FeCl(2) and di-tert-butyl peroxide (DTBP).

MATERIALS

Product Number

Brand

Product Description

429368

Sigma-Aldrich

Iron(II) chloride, AnhydroBeads^™, −10 mesh, 99.998% trace metals basis

450944

Sigma-Aldrich

Iron(II) chloride, AnhydroBeads^™, −10 mesh, 99.9% trace metals basis

450936

Sigma-Aldrich